Shooing Away Shrooms Dealers and Other Comedy Lessons: A Conversation With Lizz Winstead

There are a lot of comedians on tour today who can make fart jokes about the GOP, but very few who have legitimately changed American political discourse. Lizz Winstead is one of that rare handful.

Along with collaborator Madeleine Smithberg, she created The Daily Show. Since leaving the show in 1998 (after alleged clashes with then-host Craig Kilborn), she’s remained a major presence in American comedy and commentary: she co-created Air America Radio, bringing on talents like Rachel Maddow and Marc Maron; she sells out theaters across the country with her live performances; and she’s a prolific and well-followed tweeter.

Her first book, Lizz Free or Die (Riverhead, 2012), hits shelves this week. It’s a collection of autobiographical essays that cover her Minnesota childhood, her early career in the Twin Cities, her time in television, and a host of personal crises along the way. She’s appearing at the Tribeca Barnes & Noble on Thursday and BookCourt on Friday, and I caught up with her to talk about everything from Hüsker Dü to the hallucinogen habits of her Daily Show staff.

Before you even left Minnesota, you hung out with an array of incredible musicians, comedians, and writers who were all coming up at the same time as you. What was up with the Twin Cities in the 80s?

Dude, it was so incredible to be part of it. I don’t know if it’s the stereotypic long winter, but you had these amazing storytellers that became musicians and comedians and writers. Along with this comedy line of Joel Hodgson, Louie Anderson, Al Franken, and all of that, you had the music. You had the Replacements and Soul Asylum and Prince. You also had Michele Norris, David Carr, all these great writers coming out of it. We were this weird little club.

Bob Mould and Hüsker Dü were, of course, huge parts of that scene. How did you get Bob to write the theme music for The Daily Show?

Well, the music scene and the comedy scene really did collide. There was comedy at music venues like 7th Street Entry and this place called Goofy’s. So, sometimes we’d all be working together. The comedians would be on before the musicians and we would all gravitate to the same two or three bars where the drinks were cheapest. So, we all just got to know each other as friends. And one thing I didn’t write about in the book — and I have another book in me that I’ll write — is that I had this goofy cable-access show in Minneapolis.

We would play videos, alternative videos, and then we would have musicians. And so Bob and I had become friends and he came on the show and read my tarot cards in a garden, wearing a witch hat.

So when it was time to be able to have [The Daily Show in 1996], I was like, “Do you wanna do the theme song for this silly show I’m doing?” And he was like, “Okay.” Bob is one of those people that’s sorta like Prince, in a way, where they have these little things that they’ve written that are just locked away. Like, “I wonder what this will be for” or “I just tossed this off.”

So he had a song called “Dog on Fire” that he didn’t know what to do with. He played it for me and he was like, “What do you think about this?” And I was like, “I love this. This is amazing.” And so that’s how it came to be.

So the song was almost lost to time.

Yeah!

You’ve been doing political satire for decades now. Is it hard to find the line between satire and snark?

No, not really. If you say something about John Boehner being orange, it just lays there like a turd and doesn’t go anywhere. Or let’s say you think Eric Cantor is evil. If you just say, “Man, Eric Cantor is fucking evil,” that, to me, is just the premise. But a lot of times, people will just say, “Eric Cantor is fucking evil” in a funny way and think it’s supposed to be satire. They’re like, “Look at these evil douchebags!” and it’s like, yeah, but that’s the jumping-off point. You’ve chosen them as a target, so how are you going to show me creatively, through what Eric Cantor does, that he is an evil douchebag. Those are two different things. You know what I’m saying?

Who do you read? Where did you go for guidance on how to write this book?

As far as essays go, I love Lynda Barry and I love David Sedaris and I love Augusten Burroughs. I like dark, memoir-y kind of people. But I put everything away, because I didn’t want to– part of my biggest problem, quite frankly, was it took me three years to write the book. The first year, I spent beating myself up about whether or not I had a life that was worth telling. So then, I decided I wasn’t going to read anybody who I loved, because I was already intimidated by people who had done it and because I hadn’t done it before, I just wanted to get through it.

Your book trailer is great. I should just come out and admit that I’m a huge fan of Brian Unger. He’s fantastic.

He is. He’s an unsung hero of the Daily Show veterans. Brian’s a tremendous talent and a tremendous human being.

How did the book trailer come to be? Whose idea was it?

I needed to do a book trailer and the second I decided to do a book, anyone I know who’s written a book or is in publishing was like, “Publishing is dead, nobody buys books anymore, nobody wants to read anymore, it’s really hard, everybody just wants to read it on the Nook or on the Kindle. And I was like, “Okay, we live in a culture that needs something to do a million things.”

So I came up with the concept of the ShamWow thing to be like, “You don’t wanna read? Don’t read! It does other stuff! It can pick up dog shit!” I wrote the concept and said, “Brian, you have to do this, you’re perfect.” And he was like, “Fuck you, you’re always dragging me into something.” And I was like, “No, this’ll be fun!”

You write about telling the early Daily Show writers to stop inviting their shrooms dealer into the office. Is that all true?

Of course it’s true! Yes. It was my third day on the job. Coming from this world of comedy and standup, when you’re put in a position of power, one of my biggest fears was that I’d become a suit or “one of them” or, like, the man. I was so terrified that the writers would no longer respect me because I had control over the material. I went leaps and bounds to try and be the cool boss. The cool mom. (Laughs) But yeah, that story is 100% true.

Was the dealer a good guy? Seem nice?

I never met the dealer.

Wait. So how did you know about the shrooms, then?

Because everybody was buying shrooms! They all told me!

Oh, so you didn’t have to find out.

No, this was just like, “Hey, the shroom dealer’s coming,” and I’m like, “Oh God.” They were all talking about the shroom dealer coming up to the office. And I was like, “Fuck.” [My co-creator] Madeleine [Smithberg] was like, “We can’t have the shroom dealer coming up here. You’ve gotta talk to them.” And I was like, “You’re right.” So I said, “Hey, you guys, I don’t wanna be an asshole, but the shroom dealer? You gotta meet him at the diner. I’m sorry.”

You very pointedly don’t write about the end of your time at The Daily Show. Why is that?

I think, because, for me, my story of The Daily Show and the one that I can tell is that Madeleine and I created this thing. And [the story] is something that’s never been told. So, it was, to me, more important to talk about this interesting challenge that I faced when I got my dream show as my first show. The mistakes I made and how my passion got in the way of trusting other people and the media landscape and how the show came to be is something that, I thought, was a really interesting story to tell.

We built this kind of Model T to what Jon [Stewart] has taken and made, basically, into a vehicle that can fly into the air, into the strata of this epic brilliance. I wanted to tell that story.

If I’ve had conflict or I’ve had beef or whatever, it’s always two people’s story and the story becomes talking about that. And I felt like– why I left The Daily Show is so inconsequential to what the show is and what it’s become and how it came to be that way, that I didn’t want to have a distraction about it.

You left The Daily Show nearly 15 years ago, but you still get tagged as “Lizz Winstead, co-creator of The Daily Show.” Do you ever get tired of that?

I think you can’t avoid when something you participated in becomes bigger than you. It’s a fact of life that The Daily Show has become this force, not because of me, but because of Jon’s brilliance in taking it there. And so, being associated with something that’s awesome is sorta like– I certainly don’t care, but I also don’t want to take credit for parts that other people took and made awesome. So that’s one of the reasons that I chose to tell my part of The Daily Show, so I could put it in context.

How would you bill yourself?

I don’t even know. I would certainly say that I co-created the show. I would also say I helped launch Air America, which I’m super-proud of, because it gave so many voices a place to move on. Y’know, Marc Maron and Rachel [Maddow] and Sam Seder and these– I can’t say I launched Al. Al brought me there, basically. But also, I had this cool theater troupe that did this Off-Broadway show for two years.

I love doing standup. I loved– in hindsight, I would now probably say, “Yes, I will write another book.” I wouldn’t have said that three months ago, because the process was so intense. But now, I feel like I– once the library people wrote me a nice review, then I felt confident in my writing. But that’s so hard. Comedians view themselves, sometimes, as clowns, not as authors.

“Writer” and “author,” to me, are two separate things. It makes no sense and I know it’s probably some weird insecurity that people have. But authors need to know how to put the period inside the quotation marks and stuff.